[Setup] Can't send mail via external server

Chris Williamson chrisw at enfoldsystems.com
Sun Nov 18 22:07:46 UTC 2007


I am getting e-mail errors when trying to create users in Plone 3.0.3. Also,
the "Send this" document action link appears to work, but no e-mail arrives.

I'm evaluating Plone on my personal laptop. In Mail Settings, first I tried
to use my Gmail account and entered the following:

SMTP Server: smtp.gmail.com
SMTP Port: 587 (the port my ISP requires me to use for other SMTP servers)
ESMTP username: chriswilliamson at gmail.com
ESMTP password: (my Gmail password)

When I try to create a user, I get the following:

Error: Failed to create your account: we were unable to send your password
to your email address: (530, '5.7.0 Must issue a STARTTLS command first
i15sm7857213wxd', '"Chris Williamson" <chriswilliamson at gmail.com>')

I did a little Googling and see there are some complexities (and maybe a
bug) associated with Python, Zope and STARTTLS. So I try to simplify things
and use my ISP's SMTP server:

SMTP Server: smtp.att.yahoo.com
SMTP Port: 465 (the port AT&T Yahoo says to use)
ESMTP Username: jchriswilliamson at sbcglobal.net
ESMTP Password: (my AT&T Yahoo password)

Now when I try to add a user I get:

Error: Failed to create your account: we were unable to send your password
to your email address: Connection unexpectedly closed

Knowing that port 465 involves SSL, I try to simplify things further by
using port 25, both with and without username and password. I get the same
error.

I see in another post that I can work around this by turning off automatic
password generation, and of course I wouldn't have this problem on a
professionally hosted production site. But the 567/TLSSTART stuff makes me
wonder if I need to report a bug, because I think the current Zope MailHost
product is supposed to be able to do this. (There's a "Disable TLS" checkbox
in the ZMI.)  And the inability to connect to the AT&T server on 465 ... it
just seems I should be able to make this work.

One twist I have not mentioned: I've got Plone running on a virtual machine.
All its network connections seem to be working fine. I even set up port
forwarding and can connect to Plone from the host machine via localhost:8080
and via the Internet using my IP address and 8080. Maybe I need to set up
some additional port forwarding, so Plone on the VM can receive data back
from the external mail server? Seems unlikely though, since my normal e-mail
cilent (Evolution) doesn't need me to open ports on my router to send e-mail
via these servers.

Ideas? Thoughts?
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